{{Short description|Stimulant and NDRI drug}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | class = Stimulant; Norepinephrine–dopamine reuptake inhibitor (NDRI) | verifiedrevid = 464215530 | IUPAC_name = 1-(1-phenylpentan-2-yl)pyrrolidine | image = Prolintane.svg | image_class = skin-invert-image | image2 = Prolintane3d.png | image_class2 = bg-transparent
<!--Clinical data-->| tradename = Catovit, Katovit, Promotil, Villescon | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | legal_AU = S4 | legal_BR = B1 | legal_BR_comment = <ref>{{cite web | author = Anvisa | date = 2023-03-31 | title = RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial | language = pt-BR | publisher = Diário Oficial da União | url = https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 | access-date = 2023-08-16 | archive-date = 2023-08-03 | archive-url = https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 | author-link = Brazilian Health Regulatory Agency | trans-title = Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control | url-status = live | publication-date = 2023-04-04 }}</ref> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | routes_of_administration = By mouth, intranasal, rectal
<!--Identifiers-->| CAS_number_Ref = {{cascite|changed|cas}} | CAS_number = 493-92-5 | ATC_prefix = N06 | ATC_suffix = BX14 | PubChem = 14592 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 13930 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = EM4YZW677H | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 2111047
<!--Chemical data-->| C = 15 | H = 23 | N = 1 | smiles = CCCC(N1CCCC1)CC2=CC=CC=C2 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C15H23N/c1-2-8-15(16-11-6-7-12-16)13-14-9-4-3-5-10-14/h3-5,9-10,15H,2,6-8,11-13H2,1H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = OJCPSBCUMRIPFL-UHFFFAOYSA-N | melting_point = 133 | boiling_point = 153 }}
'''Prolintane''' is a central nervous system (CNS) stimulant<ref>{{cite journal | vauthors = Hollister LE, Gillespie HK | date = March–April 1970 | title = A new stimulant, prolintane hydrochloride, compared with dextroamphetamine in fatigued volunteers | journal = The Journal of Clinical Pharmacology and the Journal of New Drugs | volume = 10 | issue = 2 | pages = 103–109 | doi = 10.1177/009127007001000205 | pmid = 4392006 }}</ref> and norepinephrine–dopamine reuptake inhibitor (NDRI) of the phenylalkylpyrrolidine family developed in the 1950s.<ref>{{cite patent | country = GB | number = 807835 | title = New tertiary amines and their salts and process for their preparation | pubdate = 1959-01-21 | fdate = 1955-09-23 | assign1 = Dr Karl Thomae GmbH | assign2 = Boehringer Ingelheim Pharma GmbH and Co KG | url = https://patents.google.com/patent/GB807835 }}</ref> Being an amphetamine derivative, it is closely related in chemical structure to other drugs such as pyrovalerone, MDPV, and propylhexedrine, and has a similar mechanism of action.<ref>{{cite journal | vauthors = Nicholson AN, Stone BM, Jones MM | date = November 1980 | title = Wakefullness and reduced rapid eye movement sleep: studies with prolintane and pemoline | journal = British Journal of Clinical Pharmacology | volume = 10 | issue = 5 | pages = 465–472 | doi = 10.1111/j.1365-2125.1980.tb01790.x | pmc = 1430138 | pmid = 7437258 }}</ref> Many cases of prolintane abuse have been reported.<ref>{{cite journal | vauthors = Kyle PB, Daley WP | date = September 2007 | title = Domestic abuse of the European rave drug prolintane | journal = Journal of Analytical Toxicology | volume = 31 | issue = 7 | pages = 415–418 | doi = 10.1093/jat/31.7.415 | doi-access = free | pmid = 17725890 }}</ref>
Under the brand name '''Katovit''', prolintane was commercialized by the Spanish pharmaceutical company FHER until 2001. It was most often used by students and workers as a stimulant to provide energy and increase alertness and concentration.<ref name="auto">{{cite journal | vauthors = Kastner N, Islam MN, Dybek M, Roth E, Heisinger S, Holy M, Jäntsch K, Walther D, Stockner T, Baumann MH, Brandt SD, Wallach J, Sitte HH, Kudlacek O | date = December 2025 | title = Prolintane analogs as hybrid monoamine transporter ligands: Structural determinants and species differences | journal = The Journal of Biological Chemistry | volume = 301 | issue = 12 | article-number = 110903 | doi = 10.1016/j.jbc.2025.110903 | doi-access = free | pmc = 12720098 | pmid = 41197716 }}</ref> Prolintane and substituted prolintane analogs (fluoro and methyl) show DAT and NET inhibition in the low nanomolar range, which is consistent with NDRI psychostimulants such a methylphenidate.<ref name="auto"/> In addition 4-substituted analogs have SERT inhibition which correlates with amphetamine SAR such as fenfluramine.<ref name="auto"/>
== See also == * α-PVP (β-ketone-prolintane, prolintanone) * Methylenedioxypyrovalerone (MDPV) * Pyrovalerone (Centroton, Thymergix) * Phenylpropylaminopentane (PPAP)
== References == {{Reflist}}
{{Stimulants}} {{Monoamine reuptake inhibitors}} {{Phenethylamines}} {{Chemical classes of psychoactive drugs}}
Category:Alpha-Propylphenethylamines Category:Norepinephrine–dopamine reuptake inhibitors Category:Phenylethylpyrrolidines Category:1-Pyrrolidinyl compounds Category:Stimulants
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